Switching to iPhone: How To Get Your Content Into iTunes - Wait-a-Thon!

[Note: This a a Wait-A-Thon post! Comment on this post -- or any post tagged "Wait-a-Thon" -- for your chance to win a $100 iTunes Gift Card! Note that you must post with a valid and real email address so we can send you your prize -- no switching!]

More and more people are switching to the iPhone. They’re switching from Palm and Windows Mobile and even Blackberry (looking at you, Barack Obama!) smartphones to the iPhone. They’re switching carriers to get the iPhone. They’re switching off the carrier-locks just to be able to switch to the iPhone in their own, currently unsupported countries. And now that the next-gen iPhone 3G is all but upon us, and more and more regions are announcing deals to offer it, the switching is only going to get faster and more furious.

To celebrate the switchers, those who dare to phone different, the iPhone Blog wants to help you get your content off your old, perhaps restrictive and outdates systems, and onto iTunes, ready to sync to your new iPhone.

Read on to find out how!

This article assumes you’re switching from another smartphone, like Blackberry, Windows Mobile, or Palm, and are new to the iTunes + iPod (and iPhone!) ecosystem. It also assumes you're a dedicated Windows user or someone who just recently switched from Windows to the Mac and needs to transfer content to iTunes.

Since longtime iPod (and Mac) aficionados will almost certainly already be using iTunes, your iPhone will sync your existing iTunes content the same as it would any other iPod. And, hey, if you’re a Linux (or any other *nix) user, I figure you’ve kept your content open from the get-go, and already know 18 different ways to get it onto your unlocked, jailbroken iPhone...

Getting iTunes

iTunes is a free download from apple.com and required before you can activate your retail iPhone. (And if your iPhone is unlocked, required before you can easily manage and sync content). If you don't already have it, go get it now. I'll wait. Honest.

Making the Most of Your Music

When you’re moving to the iPhone and iTunes ecosystem, the first and easiest content to move over is your digital music (stuff you’ve already bought, ripped from CD, or created yourself).

Moving MP3s and WMAs

First, we have to address the monster in the room -- DRM, which technically stands for Digital (Copy) Rights Management, though Draconian Restrictive Measures may be more accurate. It's a way of locking down content ostensibly to prevent piracy but often to frustrate legitimate users. For now, if you bought music from an online store like MSN Music, Yahoo Music, Zune Marketplace, etc. it's almost certainly got DRM that will prevent you from easily moving it to iTunes. Don't worry, I'll cover ways to work around it (for legitimate purposes only!) at the end of the article.

If your music is already DRM-free you're good to go and in an iTunes/iPhone supported format like MP3, just drag it over and drop it in (or choose File - Add to Library for you old school menu-lovers). For DRM-free/unprotected WMA (Windows Media Audio, the native format of Windows Media Player) music, while iTunes won’t play it, it will automatically convert it to an iTunes-friendly format for you. (See Ripping CDs, below, for details on how to chose iTunes conversion formats).

This puts your content into a logical file structure so you can more easily find individual files later with Windows Explorer, avoids wasting space with duplicate content, and prevents iTunes from losing track of something you added (for example off a USB drive) but forgot to copy locally.

Ripping CDs

If your music is on CD, iTunes will rip it straight to either MP3 or AAC (the successor to MP3 which has less support but arguably greater potential quality). Unless you’re tone deaf, I recommend ripping to at least 256 bit. You can set this via Edit - Preferences - Advanced - Importing - Import Using and Setting (Custom).

Buying Music Online

Want to buy music for you iPhone? iTunes is the #1 retailer now and provides nearly effortless browsing and purchasing options. Just hit the iTunes Store link in the sidebar and find what you like. For reason’s we'll get into in a moment, I heavily recommend buying only iTunes Plus music, which is the higher, 256 bit quality and DRM-free.

Though Apple CEO Steve Jobs has famously said iTunes would rather sell only DRM-free music, currently, EMI and independent labels are the only source of iTunes plus music. Sadly, to try and manipulate and fragment the market, Universal, Sony BMG, and Warner Music will only provide higher-quality, DRM-free music to iTunes competitors like Amazon MP3. But if you live in the US -- or when/if they expand the service internationally -- Amazon MP3 provides an iTunes friendly, if slightly more challenging to navigate, source for legit iPhone-compatible music.

Doing Your Best With Video

Unlike music, where MP3 is a pseudo-standard, CD ripping is mostly legal, and DRM is increasingly on the way out, video formats are far more fragmented, DVD ripping is mostly verboten, and DRM shows no signs of going anywhere anytime soon.

Moving MP4s, AVIs, WMVs, FLVs, Etc.

If you’ve shot your own videos, DVR'd, or otherwise created or acquired DRM-free video content, it’s only slightly more difficult to move them to iTunes than it is music. The “slightly” part being format. With a wide variety of containers, codecs, and the need to get both audio and video into exactly the right zen-like balance, using something like the free Videora iPhone converter for Windows or iSquint for Mac (or similar application) is almost a must. Open your existing video file, choose the iPhone setting, and let it convert.

Unless you have a fast machine, get a tasty beverage because it will take a while. And make sure you test a sample first, to prevent wasting a lot of time if your settings are off.

Already have, or already converted video content? Drag it into iTunes same as you did your music.

(Note: since iTunes doesn’t store video-type meta data in the video file itself, but rather in the iTunes database, if you want to have movies, TV shows, and music videos all filed in the right place, you’ll have to individually set them in each file’s properties under the Video tab.)

Ripping DVDs

Unlike music, where various “fair use” provisions exist that allow, in many jurisdictions, for you to rip your CDs to your computer, the DVD lobby has succeeded in making DVD ripping illegal in many parts -- the reason iTunes doesn’t provide that type of functionality itself.

If, however, you live in a place (or mindset?) that says when you legally buy a movie or TV show on DVD, you should be able to watch it regardless of whether its stays on a disk or moves to your hard drive, then open source software like Handbrake is your best friend. Handbrake will rip most DVDs straight to iPhone format, and add them to iTunes, in just a couple easy steps (navigate to your DVDs video directory, select the iPhone default, and let it rip!).

Bonus tip: make sure, especially when dealing with older movies, full screen movies, or TV shows, that you preview the video and choose de-interlace when necessary to prevent nasty scan-lines from showing up on your digitized video.

Buying Videos

Depending on what country you live in, iTunes provides movie rentals and downloadable movies, music videos, and TV shows. These are DRM-locked (see below) but perfectly compatible with the iPhone. Selection varies greatly from region to region, and some networks -- most famously NBC -- don’t see eye to eye with Apple’s less anti-consumer model, but until Apple unleashes its own DVR, this is the easiest way to get legit video on your iPhone.

Love podcasts, like our very own Phone Different podcast? Subscribe directly from the iTunes Store (or from the Subscribe via iTunes link from your favorite podcast's homepage). They’re free, come in audio and video (even HD!) and download straight into iTunes. While you’re there, be sure to check out iTunes University (also under the iTunes Store) for loads of free, and highly educational audio and video, from lectures to speeches to commencement addresses.

Dealing with DRM-Hell

Now for the hard part. If you previously bought music locked down with DRM, especially the more onerous DRM systems like PlaysForSure (or in MSN Music's case, PlaysNoMore!), there’s a little more work involved.

The Problem With DRM

What’s wrong with DRM? It does nothing to prevent real pirates (many of whom mass-produce content on boats in international waters or distribute online via massive criminal networks) and everything to frustrate regular, legitimate users who just want to upgrade their computers or move their content from one device or room to another.

We’ve all read the stories, from Google Video to Major League Baseball, to MSN Music. People, in good faith, spend their hard-earned money to buy the content they love, only to later get notification that the service they chose, from the vendors they trusted, will no longer “authorize” them to play back that content.

Imagine Tower Records going out of business and some men in black showing up to re-possess all the CDs and LPs (yes, we’re old enough to remember LPs, thank you!) that you ever bought from that store.

Sounds ridiculous, doesn’t it? But with digital content it's happened before and will happen again. Windows Media Player has also been known to automatically DRM music you rip from your own CDs if you’re not paying attention to the preference settings. So, if you’re stuck with previously bought or ripped DRM music, what can you do?

The Analog Hole

While from time to time DRM-stripping applications show up on the web, most DRM services are bound by their contracts with the big media companies to update the DRM as quickly as possible to render any circumvention obsolete. This makes DRM-stripping unreliable.

A more dependable, although technically “lossy” solution (i.e. some loss of quality will occur, though it will likely be negligible to all but audiophiles), is the infamous “analog hole”.

For music, simply use your old software (e.g. Window Media Player) to burn your DRM-locked WMA (or other format) music to playable CDs, and then use iTunes to rip those CDs back into digital format (preferably MP3).

Voila, the music you paid for, now ready for the device you chose to use it on.

Video is more of a challenge. If you’re an advanced user and have a Media Center PC (or two PCs, depending), with analog output and input, you can try routing your DRM-locked video out and back in, re-recording it like you would a VHS tape or analog cable TV signal. Provided you could then navigate the “black art” of video and audio containers and codecs, using something like the aforementioned Videora, for example, you could convert the captured video into iTunes/iPhone friendly MP4 H.264 format.

While Apple has among the most progressive DRM systems on the market, with the ability to sync any number of iPods to your iTunes, and authorize up to 5 computers to play your DRM-locked content (and the ability to call Apple for one-time re-downloads and re-authorizations should something go wrong), it’s vital to remember to BACK UP you iTunes content. USB hard drives are now ridiculously cheap and ridiculously big, so get one and copy everything to it, and update the copy regularly.

Also, burn playable CDs of all DRM-locked music and rip them back into iTunes so that, in case of system loss, re-install, or other catastrophic problems, you don’t have to worry about getting locked out of your own music.

Conclusion

Well, there they are, my tips and tricks for getting your content off the old and outdated and onto iTunes just in time for your brand new iPhone. But try as I might, I know our readers -- the real content ninjas -- have a whole host of sneaky black magic all their own.

Reader comments

Switching to iPhone: How To Get Your Content Into iTunes - Wait-a-Thon!

It's perfect time to make a few plans for the longer term and it is time to be happy. I've learn this put up and if I may just I wish to counsel you few fascinating issues or suggestions. Maybe you can write subsequent articles relating to this article. I want to learn even more issues approximately it!

It's appropriate time to make a few plans for the long run and it is time to be happy. I've learn this publish and if I may just I wish to recommend you some fascinating issues or advice. Maybe you could write subsequent articles regarding this article. I wish to read even more things about it!

I just could not leave your site prior to suggesting that I actually loved the usual information a person provide to your visitors? Is gonna be again incessantly in order to investigate cross-check new posts

Very great post. I just stumbled upon your weblog and wished to say that I have really enjoyed surfing around your blog posts. In any case I will be subscribing for your feed and I hope you write again very soon!

I believe this is among the so much important information for me. And i'm happy studying your article. But should statement on few normal things, The web site taste is ideal, the articles is actually excellent : D. Excellent job, cheers

That is very fascinating, You are an overly professional blogger. I've joined your feed and stay up for in search of more of your fantastic post. Additionally, I've shared your site in my social networks

Undeniably believe that that you said. Your favorite reason appeared to be at the web the easiest factor to be aware of. I say to you, I certainly get annoyed whilst folks consider concerns that they plainly do not recognize about. You controlled to hit the nail upon the top and outlined out the whole thing with no need side-effects , people can take a signal. Will likely be again to get more. Thank you

Great work! This is the kind of info that are supposed to be shared around the web. Disgrace on the search engines for no longer positioning this submit upper! Come on over and discuss with my site . Thanks =)

I do not even understand how I finished up here, but I thought this submit was once great. I do not recognize who you might be but certainly you are going to a well-known blogger should you aren't already. Cheers!

Thanks a bunch for sharing this with all people you actually recognize what you are speaking about! Bookmarked. Please additionally talk over with my web site =). We may have a link change agreement among us

Hello there, simply become aware of your blog via Google, and located that it is really informative. I'm gonna watch out for brussels. I'll appreciate if you happen to continue this in future. Many folks will likely be benefited from your writing. Cheers!

Hello there, just become aware of your blog thru Google, and found that it's really informative. I am gonna be careful for brussels. I'll be grateful should you continue this in future. Numerous people might be benefited from your writing. Cheers!

Somebody necessarily help to make seriously posts I might state. That is the very first time I frequented your website page and so far? I surprised with the research you made to create this particular put up amazing. Magnificent task!

I beloved up to you'll receive performed proper here. The sketch is attractive, your authored subject matter stylish. nevertheless, you command get got an impatience over that you want be turning in the following. in poor health definitely come further previously again since exactly the same just about very incessantly within case you protect this increase.

You really make it appear really easy together with your presentation however I find this matter to be really one thing that I believe I would by no means understand. It kind of feels too complex and very extensive for me. I am looking ahead on your next submit, I will try to get the hold of it!

I just could not go away your site before suggesting that I really loved the standard information an individual supply for your visitors? Is going to be back ceaselessly to investigate cross-check new posts

I used to be suggested this website through my cousin. I am now not positive whether or not this post is written by means of him as no one else know such special approximately my difficulty. You're amazing! Thank you!

It's the best time to make some plans for the future and it is time to be happy. I've read this publish and if I may I wish to suggest you few fascinating things or suggestions. Perhaps you could write next articles referring to this article. I wish to read even more things about it!

hello there and thanks in your information ? I've certainly picked up something new from proper here. I did then again expertise several technical points using this web site, since I skilled to reload the web site a lot of instances previous to I could get it to load correctly. I had been brooding about if your hosting is OK? Not that I am complaining, but slow loading cases occasions will often affect your placement in google and can injury your high-quality ranking if advertising and marketing with Adwords. Well I am including this RSS to my email and can look out for much more of your respective intriguing content. Make sure you update this again very soon..

Very good post! If you eat well balanced meals with as many fresh unprocessed foods as possible, then you probably won't need to take many vitamins or supplements. The problem is that many of us can't always eat healthy foods. Some of us eat more fast food than anything else. But as you mentioned, ask your health care provider about what is right for you.

ActiveSync makes its debut with iPhone 2.0, and doesn’t function on the older, 1.x firmware, so if you intend to use it, make sure you have an iPhone 3G or have updated your original iPhone (2G) to the latest firmware as of July 11, 2008. To setup Exchange ActiveSync, tape the logo for it. If you’re using Exchange 2007 on the back end, you may be able to automatically set up your account. If you can’t, or are using an old version of Exchange — or just in general due to the complex and fussy nature of setting up an Exchange account in general — you’re best practice is to check with your Exchange administrator (or hosted service provider).

I really need help syncing my itunes library to my iphone which has an unsupported carrier- T mobile. Itunes will not let me activate my iphone bcos it has an unsupported carrier it says. My iphone is currently unlocked and jailbroken. Please help...

If you want to install iPod Video Converter you can follow this guide: http://www.mconverter.net
iPod Video Converter for Mac is powerful, easy-to-use Mac video conversion software adapted to be installed for Mac users which convert video file between all popular video formats.

Don't forget that you can get free commercial content (music, TV shows, etc) from the iTunes Store every Tuesday. I find it a great way to discover new artists (e.g. Duffy) and shows (e.g. New Amsterdam)

I have used a Palm/Treo since my fist Palm III in '99. I tried a WM device a few years ago and found that I couldn't get used to the OS. I demo'ed an iPhone and found it incredibly intuitive. With the SDK and upcoming 3G, I will definitely be switching! Can't wait for my iPhone to harmonize with my iMac and Macbook Pro!

I used to get almost all my music through iTunes. Now, I'm kind of split between Amazon MP3 and iTunes, but I usually choose whatever source has the music and if both, which one is selling without all the DRM nonsense (i.e. iTunes Plus or everything at Amazon MP3)

I'll be switching from a Palm Treo 700p when the 3G iPhone finally rolls out but since I'm a Mac user and iPod owner I'm already set up in iTunes, iCal, Safari and Address Book. The only thing I've got to do to switch is get rid of my Verizon contract, thank goodness for data overages! :D

I really didn't like iTunes when I switched to OSX. Foobar was pretty much everything I needed when I used windows.
But iTunes is imho the best podcast downloader out there.
Concerning the music part: I got used to it and pretty much like it now :)

Good advice on ripping DVD's and converting to iTunes format. I was looking for something that did this all in one program since before I was using a seperate converter and ripper and neither worked that great.
Can anyone suggest a converter that will convert PSP compatable video's to iPhone compatable video's? Thanks!

Since I already had several iPods before getting an iPhone, getting music on my phone was no problem. Video is also a breeze. I love being able to rent movies for plane flights. Synching Contacts with Outlook is a bit more problematic as the sync process has a few quirks in it (synching changes back up from the iPhone messes up the desktop Contact records in my Outlook 2007).
Anyway, Wait-a-Thon!

This article was expressly about media content (audio and video) and iTunes, but if PIM content and Outlook are popular requests (and it looks like they are) we can certainly look into covering that in a future article!

Thanks, it is good see the basic iTunes content but I agree with burnsaa, what about the smartphone info like contacts & tasks? I currently use a Palm Treo and I am curious how I can get the Tasks or To Dos functionality on the iPhone along with office documents, password safe, list managers (SplashShopper) etc.

Although it will probably solved after 3rd-party apps become available, is there currently any easy way to store documents (Word/Excel) to the phone (as opposed to a 3rd party web-app like Google Docs)??